Sulfuric acid magnesium salt (1:1) → HCID 57564373, compound

HRID 1726524Notes

Reaction equation

HRID 1726524 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:11][CH2:10][CH:9]([NH:12][S:13]([C:16]2[C:25]3[CH2:24][CH2:23][CH2:22][CH2:21][C:20]=3[C:19]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:8][CH2:7]1)=[O:5])[CH3:2].S([O-])([O-])(=O)=[O:37].[Mg+2].[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([N:6]1[CH2:7][CH2:8][CH:9]([NH:12][S:13]([C:16]2[C:25]3[CH2:24][CH2:23][CH2:22][C:21](=[O:37])[C:20]=3[C:19]([NH:26][C:27](=[O:35])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=3[CH3:34])=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 516875Potassium PermanganateHCID 11386472HCID 11386472, compound

Product 1

HCID 57564373HCID 57564373, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-[4-(2-Methyl-benzoylamino)-5,6,7,8-tetrahydro-naphthalene-1-sulfonylamino]-piperidine-1-carboxylic acid ethyl ester (1.12 g, 2.24 mmol) was dissolved in acetone (25 mL) and a 15% aqueous solution of magnesium sulfate(2.5 mL). The solution was cooled in an ice bath and potassium permanganate (1.9 g, 12.3 mmol) was added and the solution was stirred for 15 min at which time the solution was allowed to warm to room temperature and stirred for 3 hr. The solution was concentrated and diluted with 150 mL water. The product was exhaustively extracted from the aqueous layer with methylene chloride. The organic was then washed with brine, dried over anhydrous magnesium sulfate, concentrated and purified on silica (Isco flash column, 0 to 40% ethyl acetate in hexane). The title compound was isolated in 17% yield (200 mg).

Workup

  1. temperatureThe solution was cooled in an ice bath
  2. stirringstirred for 3 hr
  3. concentrationThe solution was concentrated
  4. additiondiluted with 150 mL water
  5. extractionThe product was exhaustively extracted from the aqueous layer with methylene chloride
  6. washThe organic was then washed with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated
  9. custompurified on silica (Isco flash column, 0 to 40% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2e85929bb6c04a85b44b3570f068c436
Source dataset
uspto-grants-2009_02
Patent number
US07491827B2

Reaction notes

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